952514-79-3|(4-(1-Phenyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid| Ambeed

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Quality Control of [ 952514-79-3 ] Purity: 96% SDS Specification

COA

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Product Details of [ 952514-79-3 ]

CAS No. :	952514-79-3
Formula :	C₁₉H₁₅BN₂O₂
M.W :	314.15
SMILES Code :	OB(C1=CC=C(C2=NC3=CC=CC=C3N2C4=CC=CC=C4)C=C1)O
MDL No. :	MFCD11045057
InChI Key :	PBSIVXAPTBHFFV-UHFFFAOYSA-N
Pubchem ID :	53249779

Safety of [ 952514-79-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 952514-79-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	24
Num. arom. heavy atoms	21
Fraction Csp3	0.0
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	96.33
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	58.28 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.66
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.37
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.61
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.4
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.01

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.54
Solubility	0.009 mg/ml ; 0.0000286 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.57
Solubility	0.0084 mg/ml ; 0.0000267 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.99
Solubility	0.000319 mg/ml ; 0.00000102 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.62 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.52

Application In Synthesis of [ 952514-79-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 952514-79-3 ]

[ 952514-79-3 ] Synthesis Path-Downstream 1~35

1
[ 790674-48-5 ]
[ 952514-79-3 ]
[ 1274565-72-8 ]

References: [1]Journal of Materials Chemistry,2011,vol. 21,p. 1846 - 1851.

2
[ 952514-79-3 ]
[ 171408-84-7 ]
[ 1274565-70-6 ]

References: [1]Journal of Materials Chemistry,2011,vol. 21,p. 1846 - 1851.

3
[ 2620-76-0 ]
[ 952514-79-3 ]

References: [1]Journal of Materials Chemistry,2011,vol. 21,p. 1846 - 1851.

4
[ 24672-71-7 ]
[ 952514-79-3 ]
[ 1283598-73-1 ]

References: [1]Journal of Materials Chemistry,2011,vol. 21,p. 2957 - 2964.

5
[ 808758-81-8 ]
[ 952514-79-3 ]
[ 1226993-72-1 ]

References: [1]Advanced Functional Materials,2010,vol. 20,p. 399 - 408.

6
[ 952514-79-3 ]
[ 56990-02-4 ]
[ 1226993-71-0 ]

References: [1]Advanced Functional Materials,2010,vol. 20,p. 399 - 408.

7
[ 952514-79-3 ]
[ 56990-02-4 ]
[ 1226993-70-9 ]

References: [1]Advanced Functional Materials,2010,vol. 20,p. 399 - 408.

8
[ 1153-85-1 ]
[ 952514-79-3 ]
[ 1294411-24-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 6h;Inert atmosphere; Reflux;	3-BrPCz (6.44g, 0.02mol) was added to a three-necked flask, BnImBA (6.91g, 0.022mol), aqueous potassium carbonate (38.3g, 0.06mol), 100ml of toluene, 50ml of ethanol; under nitrogen with stirring was added Pd (PPh3)4(0.23g, 0.2mmol), after the replacement with nitrogen, the reaction was refluxed for 6 hours; after completion of the reaction, was cooled to room temperature, the layers were separated and the organic phase was washed with saturated aqueous sodium chloride solution until neutral, dried over anhydrous sodium sulfate and filtered to give a brown liquid; The solvent was removed by rotary evaporation, silica gel column, eluent VPetroleum ether: VEthyl acetate= 1: 1 was purified to obtain the white solid in 80% yield.

References: [1]Patent: CN104370904,2016,B .Location in patent: Paragraph 0062; 0067-0069.
[2]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 841 - 846.

9
[ 952514-79-3 ]
[ 934545-80-9 ]
[ 1334036-93-9 ]

References: [1]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 841 - 846.

10
[ 952514-79-3 ]
[ 57103-20-5 ]
[ 1258780-50-5 ]

References: [1]Journal of Nanoscience and Nanotechnology,2011,vol. 11,p. 1373 - 1376.

11
[ 952514-79-3 ]
[ 1289472-57-6 ]
[ 1289472-71-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate monohydrate; tris-(o-tolyl)phosphine; In 1,4-dioxane; water; toluene; for 5h;Reflux;	Example 7 [6-(1-Phenyl-1H-benzimidazol-2-yl)phenyl]-8,8-dimethyl-8H-indolo[3,2,1-de]acridine 0.27 g (0.9 mmol) of tri-o-tolylphosphine and then 33.5 mg (0.15 mmol) of palladium(II) acetate are added with vigorous stirring to a degassed suspension of 10.1 g (28 mmol) of 6-bromo-8,8-dimethyl-8H-indolo[3,2,1-de]-acridine and 9.42 g (30 mmol) of benzimidazoleboronic acid and 7.8 g (31.5 mmol) of potassium phosphate hydrate in a mixture of 7.5 ml of dioxane, 15 ml of toluene and 18 ml of water. After heating under reflux for 5 h, the mixture is allowed to cool. The precipitate is filtered off with suction, washed three times with 10 ml of ethanol/water (1:1, v:v) and three times with 5 ml of ethanol, subsequently dried in vacuo and recrystallised from dioxane. Yield: 12.46 g (22.5 mmol), 81% of theory, purity according to 1H-NMR about 99.9%.

References: [1]Patent: US2012/202997,2012,A1 .Location in patent: Page/Page column 89.

12
[ 952514-79-3 ]
[ 1290058-18-2 ]
[ 1290058-19-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium phosphate monohydrate; tris-(o-tolyl)phosphine;palladium diacetate; In 1,4-dioxane; water; toluene; for 5h;Reflux;	Example 21 8,8-Diphenyl-6-[4-(1-phenyl-1H-benzoimidazol-2-yl)-phenyl]-8H-indolo[3,2,1-de]acridine 0.27 g (0.9 mmol) of tri-o-tolylphosphine and then 33.5 mg (0.15 mmol) of palladium(II) acetate are added with vigorous stirring to a degassed suspension of 13.6 g (28 mmol) of 3-bromo-8,8-diphenyl-8H-indolo[3,2,1-de]-acridine, 9.42 g (30 mmol) of benzimidazoleboronic acid and 7.8 g (31.5 mmol) of potassium phosphate hydrate in a mixture of 7.5 ml of dioxane, 15 ml of toluene and 18 ml of water. After heating under reflux for 5 h, the mixture is allowed to cool. The precipitate is filtered off with suction, washed three times with 10 ml of ethanol/water (1:1, v:v) and three times with 5 ml of ethanol, subsequently dried in vacuo and recrystallised from dioxane. Yield: 16 g (23 mmol), 85% of theory, purity according to 1H-NMR about 99.9%.

References: [1]Patent: US2012/202997,2012,A1 .Location in patent: Page/Page column 95.

13
[ 952514-79-3 ]
[ 1425793-65-2 ]

References: [1]Patent: US2013/48956,2013,A1 .

14
[ 952514-79-3 ]
[ 1425793-66-3 ]

References: [1]Patent: US2013/48956,2013,A1 .

15
[ 952514-79-3 ]
[ 1425793-69-6 ]

References: [1]Patent: US2013/48956,2013,A1 .

16
[ 952514-79-3 ]
[ 1425793-70-9 ]

References: [1]Patent: US2013/48956,2013,A1 .

17
[ 952514-79-3 ]
[ 1425793-63-0 ]
[ 1425793-64-1 ]

Yield	Reaction Conditions	Operation in experiment
9.5 g	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 6h;Inert atmosphere; Reflux;	Synthesis Example 2 Synthesis of Compound 1-26 Following the above procedure, Suzuki coupling of 6.7 g of 9-bromo-11-acetyl-11H-benzo[a]carbazole and 14.0 g of 4-(1-phenyl-1H-benzo [d]imidazol-2-yl) phenylboronic acid were stirred together in 30 ml of toluene. To this was added 0.02 g of tetrakis(triphenylphosphine)palladium, 6.9 g of potassium carbonate and 10 ml of aqueous ethanol were added and refluxed under nitrogen for 6 h. The reaction was quenched with water and the toluene layer was removed and passed through a celite column. The organic layers were combined and then evaporated in a rotary evaporator under vacuum to yield 9.5 g of 11-acetyl-3-[4-(1-phenyl-1H-benzo[d] imidazol-2-yl) phenyl]-11H-benzocarbazole as a white solid.

References: [1]Patent: US2013/48956,2013,A1 .Location in patent: Paragraph 0069.

18
[ 952514-79-3 ]
[ 1425793-67-4 ]
[ 1425793-68-5 ]

Yield	Reaction Conditions	Operation in experiment
4.6 g	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 6h;Inert atmosphere; Reflux;	Synthesis Example 3 Synthesis of Compound 1-11 Following the above procedure, Suzuki coupling of 3.4 g of 7-acetyl-12-bromo-7H-dibenzo [a,g]carbazole and 3.8 g of 4-(1-phenyl-1H-benzo [d]imidazol-2-yl) phenylboronic acid were stirred together in 30 ml of toluene. To this was added 0.01 g of tetrakis(triphenylphosphine)palladium, 2.7 g of potassium carbonate and 10 ml of aqueous ethanol were added and refluxed under nitrogen for 6 h. The reaction was quenched with water and the toluene layer was removed and passed through a celite column. The organic layers were combined and then evaporated in a rotary evaporator under vacuum to yield 4.6 g of 7-acetyl-12-[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]-7H-dibenzo [a,g]carbazole as a white solid.

References: [1]Patent: US2013/48956,2013,A1 .Location in patent: Paragraph 0073.

19
[ 38573-63-6 ]
[ 952514-79-3 ]
[ 1425793-71-0 ]

Yield	Reaction Conditions	Operation in experiment
10.5 g	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 6h;Inert atmosphere; Reflux;	Synthesis Example 4 Synthesis of Compound 1-35 Following the above procedure, Suzuki coupling of 7.4 g of 9-Acetyl-3,6-dibromocarbazole and 14.0 g of 4-(1-phenyl-1H-benzo [d]imidazol-2-yl) phenylboronic acid were stirred together in 30 ml of toluene. To this was added 0.03 g of tetrakis(triphenylphosphine)palladium, 7.0 g of potassium carbonate and 10 ml of aqueous ethanol were added and refluxed under nitrogen for 6 h. The reaction was quenched with water and the toluene layer was removed and passed through a celite column. The organic layers were combined and then evaporated in a rotary evaporator under vacuum to yield 10.5 g of 9-acetyl-3,6-bis[4-(1-phenyl-1H-benzo [d]imidazol-2-yl) phenyl]-9H-carbazole as a white solid.

References: [1]Patent: US2013/48956,2013,A1 .Location in patent: Paragraph 0078.

20
[ 38573-63-6 ]
[ 952514-79-3 ]
[ 1425793-72-1 ]

References: [1]Patent: US2013/48956,2013,A1 .

21
[ 177775-86-9 ]
[ 952514-79-3 ]
[ 1425793-60-7 ]

Yield	Reaction Conditions	Operation in experiment
8.3 g	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 6h;Inert atmosphere; Reflux;	Synthesis Example 1 Synthesis of Compound 1-17 A mixture of 5.8 g of 9-Acetyl-3-bromoocarbazole and 14.0 g of 4-(1-phenyl-1H-benzo [d]imidazol-2-yl) phenylboronic acid were stirred together in 30 ml of toluene. To this was added 0.02 g of tetrakis (triphenylphosphine) palladium, 6.9 g of potassium carbonate and 10 ml of aqueous ethanol were added and refluxed under nitrogen for 6 h. The reaction was quenched with water and the toluene layer was removed and passed through a celite column. The organic layers were combined and then evaporated in a rotary evaporator under vacuum to yield 8.3 g of 9-acetyl-3-[4-(1-phenyl-1H-benzo [d]imidazol-2-yl) phenyl]-9H-carbazole as a white solid.

References: [1]Patent: US2013/48956,2013,A1 .Location in patent: Paragraph 0065.

22
[ 952514-79-3 ]
3-(2'-bromo-[1,1'-biphenyl]-2-yl)-9-phenyl-9H-carbazole [ No CAS ]
9-phenyl-3-(4"-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1':2',1"-terphenyl]-2-yl)-9H-carbazole [ No CAS ]

References: [1]Journal of Materials Chemistry C,2014,vol. 2,p. 8554 - 8563.

23
[ 586-76-5 ]
[ 952514-79-3 ]

References: [1]Journal of Materials Chemistry C,2014,vol. 2,p. 9858 - 9865.

24
[ 586-75-4 ]
[ 952514-79-3 ]

References: [1]Journal of Materials Chemistry C,2014,vol. 2,p. 9858 - 9865.
[2]Patent: CN104073249,2016,B .
[3]Patent: CN104030988,2016,B .
[4]Patent: TWI631109,2018,B .

25
[ 359427-13-7 ]
[ 952514-79-3 ]

References: [1]Journal of Materials Chemistry C,2014,vol. 2,p. 9858 - 9865.
[2]Patent: CN104073249,2016,B .
[3]Patent: CN104030988,2016,B .
[4]Patent: TWI631109,2018,B .

26
[ 5419-55-6 ]
[ 2620-76-0 ]
[ 952514-79-3 ]

Yield	Reaction Conditions	Operation in experiment
74%	With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20℃;Inert atmosphere;	Synthesis of Compound 15-5 Under the protection of nitrogen, compound 15-4 (10.6g, 29mmol) and dry tetrahydrofuran (100 ml) were added into a three-necked flask, cooling to -78 C. Then the syringe is injected at 2.5 mol per liter n-BuLi in hexane solution (20 ml, 50mmol) with stirring, then adding triisopropyl borate (8.1g, 43mmol), continuously stirring at this temperature for 1 hour, then slowly to room temperature, stirring overnight under the protection of nitrogen. Reaction end, to the reaction solution is poured into 2N in a dilute hydrochloric acid solution, ethyl acetate extraction three times and, combined with the phase, salt water and water washing sequentially, and then drying with anhydrous sodium sulfate. To remove the solvent, the crude product with ethyl acetate and hexane recrystallization to obtain 8.3g white solid, yield is 74%.

References: [1]Patent: CN104073249,2016,B .Location in patent: Paragraph 0065; 0073; 0074.
[2]Journal of Materials Chemistry C,2014,vol. 2,p. 9858 - 9865.

27
[ 952514-79-3 ]
9-(4-bromophenyl)-14-phenyl-9,14-dihydrodibenzo[a,c]phenazine [ No CAS ]
9-phenyl-14-(4'-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1'-biphenyl]-4-yl)-9,14-dihydrodibenzo[a,c]phenazine [ No CAS ]

References: [1]Journal of Materials Chemistry C,2014,vol. 2,p. 9858 - 9865.

28
[ 87199-17-5 ]
[ 952514-79-3 ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

29
(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid MIDA ester [ No CAS ]
[ 952514-79-3 ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

30
[ 1072960-66-7 ]
[ 952514-79-3 ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

31
[ 952514-79-3 ]
C₃₆H₂₀Br₂N₂S [ No CAS ]
C₇₄H₄₆N₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 24h;Reflux;	The intermediate F obtained from the step 6), 4-(1-Phenyl-1H-benzo[d]imidazol-2-yl)phenylboronic acid, Pd(PPh3)4, and K2CO3 were dissolved in anhydrous THF and a small amount of water, followed by reflux for 24 hours. After the completion of the reaction, the resultant product was cooled to room temperature, extracted with CH2Cl2, and washed with water. From the extract, a small amount of water was removed by anhydrous MgSO4, followed by vacuum-filtration. Then, the product obtained after concentration of an organic solvent was purified by column chromatography to give a required compound 27 (yield: 57%).

References: [1]Patent: US2015/307514,2015,A1 .Location in patent: Paragraph 0084-0085.

32
[ 607-68-1 ]
[ 952514-79-3 ]
2,4-bis[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]quinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,4-dioxane; water; at 100℃; for 12h;Inert atmosphere;	General procedure: 2,4-Dichloroquinazoline (5 g, 25 mmol), aryl-boronic acid, palladium acetate (113 mg, 0.5 mmol), triphenylphosphine (264 mg, 1 mmol) and potassium carbonate (10.4 g, 75.4 mmol) were suspended in a mixture of 1,4-dioxane (60 mL) and water (30 mL) in a three-necked, round-bottomed flask with tightly sealed. The mixture was stirred and heated at 100 C for 12 h under nitrogen atmosphere. After cooling to room temperature, CH2Cl2 (50 mL) and water (50 mL) were added. The aqueous layer was extracted with CH2Cl2 (3 x 20 mL). The combined organic layers were washed by brine (3 x 30 mL), dried over anhydrous sodium sulfate and solvents were removed under reduced pressure to yield the crude product as a light yellow solid, which was further purified by recrystallization (dichloromethane/ethanol) to give pureproduct. 2,4-Bis[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]quinazoline (BBIQz) was synthesized according to the general procedure from 2,4-dichloroquinazoline (5 g, 25 mmol) and 1 (55.4 mmol) in 71% isolated yield. 1H NMR (500 MHz, CDCl3, delta): 8.62 (d, J 8.5 Hz, 2H), 8.12 (d, J 8.5 Hz, 1H), 8.06 (d, J 8.5 Hz, 1H), 7.93 (t, J 7.0 Hz, 2H), 7.89 (t, J 7.5 Hz, 1H), 7.85-7.81 (m, 4H), 7.74 (d, J 9.5 Hz, 2H), 7.58-7.47 (m, 7H), 7.42-7.34 (m, 6H), 7.33-7.27 (m, 4H); 13CNMR (125 MHz, CDCl3, delta): 159.4, 152.1, 152.0, 151.5, 143.1, 143.1,138.9, 138.3, 137.5, 137.4, 137.0, 136.9, 133.9, 131.8, 131.6, 130.2, 130.1,130.0, 129.7, 129.5, 129.3, 128.9, 128.6, 128.5, 127.5, 127.5, 126.8, 123.7, 123.5, 123.3, 123.1, 121.6, 120.0, 120.0, 110.6, 110.5; MS (m/z,EI) Calcd for C46H30N6 666.25, found: 666.20. Anal. calcd. for C46H30N6: C 82.86, H 4.54, N, 12.60; Found: C 82.74, H 4.53, N, 12.61.

References: [1]Dyes and Pigments,2016,vol. 125,p. 299 - 308.

33
[ 607-68-1 ]
[ 952514-79-3 ]
2-chloro-4-[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]quinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,4-dioxane; water; at 100℃; for 12h;Inert atmosphere;	General procedure: 2,4-Dichloroquinazoline (5 g, 25 mmol), aryl-boronic acid, palladium acetate (113 mg, 0.5 mmol), triphenylphosphine (264 mg, 1 mmol) and potassium carbonate (10.4 g, 75.4 mmol) were suspended in a mixture of 1,4-dioxane (60 mL) and water (30 mL) in a three-necked, round-bottomed flask with tightly sealed. The mixture was stirred and heated at 100 C for 12 h under nitrogen atmosphere. After cooling to room temperature, CH2Cl2 (50 mL) and water (50 mL) were added. The aqueous layer was extracted with CH2Cl2 (3 x 20 mL). The combined organic layers were washed by brine (3 x 30 mL), dried over anhydrous sodium sulfate and solvents were removed under reduced pressure to yield the crude product as a light yellow solid, which was further purified by recrystallization (dichloromethane/ethanol) to give pureproduct.
53 g	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 16h;Reflux;	30 g of 2,4-dichloroquinazoline, 47.35 g of 4- (1-phenyl-1H-benzo[d] imidazol-2-yl) 1-phenyl-1H-benzo [d] imidazol-2-yl) phenylboronicacid, 8.7 g of tetrakis (triphenylphosphine) palladium, 450 ml of toluene, 66 ml of ethanol and 200 Ml of a 2M aqueous solution of potassiumcarbonate was added to a 500 ml flask and refluxed for 16 hours.The reactiongave a solid which wasquenched with water andthe solid separatedoff. Afterheating with toluene and dissolving in hexane, 53 g of a light yellow solid was obtained.
53 g	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 16h;Reflux;	30 g of 2,4-Dichloroquinazoline and 47.35 g of 4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenylboronic acid (4-( 1-phenyl-1H-benzo[d]imidazol-2-yl)phenylboronic acid), 8.7 g of tetrakis(triphenylphosphine)palladium, 450 ml of toluene, 66 ml of ethanol and 200 A mixture of 2 M aqueous solutions of potassium carbonate was added to a 500 ml flask and refluxed for 16 hours. The reaction resulted in the formation of a solid. After quenching the reaction with water, the solid was separated and dissolved by heating with toluene and precipitated with hexane to give 53 g of pale yellow solid.

References: [1]Dyes and Pigments,2016,vol. 125,p. 299 - 308.
[2]Patent: CN106957272,2017,A .Location in patent: Paragraph 0086; 0087.
[3]Patent: TWI603960,2017,B .Location in patent: Paragraph 0065; 0066.

34
[ 607-68-1 ]
[ 952514-79-3 ]
4-[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]-2-[3-(triphenylen-2-yl)phen-3-yl]quinazoline [ No CAS ]

References: [1]Dyes and Pigments,2016,vol. 125,p. 299 - 308.

35
[ 952514-79-3 ]
[ 112865-06-2 ]
C₅₈H₃₆N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 5h;Inert atmosphere; Reflux;	Synthesis of Compound 15 In the single-necked flask, the compound 15-2 (0.3g, 0 . 68mmol), is added to compound 15-5 (0.6g, 1 . 78mmol), tetrahydrofuran (20 ml) and 2MK 2 CO 3 aqueous solution (10 ml), under the protection of nitrogen, by adding four (triphenylporphyrin phosphorus) palladium (10 mg, 0 . 0075mmol), then heating reflux for 5 hours, the reaction end, cooling, extraction with methylene chloride three times, the organic layer is dried with anhydrous sodium sulfate, the rotating removal of the organic solvent, the crude product is subjected to a column chromatography purification, get 0.4g yellow solid, yield is 72%

References: [1]Patent: CN104073249,2016,B .Location in patent: Paragraph 0065; 0075; 0076.

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CAS No.: 952514-79-3

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CAS No.: 952514-79-3

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